Gates Hotel

Long associated with spring break excess and the literary world (Hemingway lived and wrote here for years), Key West is undergoing a sort of hipster sanding down: New cocktail lounges, third-wave coffee bars, and boutique hotels—including the new 100-room Gates Hotel (slated to open in early 2015)—are adding a little polish to the notoriously eccentric island.

The hotel is a midcentury-esque sprawl located just steps from the Gulf of Mexico. Cuba was the primary inspiration, a theme that plays out everywhere from the room décor (think whitewashed walls, weathered leather, and pops of aquamarine and burnt orange) to the weekly Cuban pig roasts. There’s even a cigar garden, where you can smoke a stogie or learn to roll your own in a class with the Rodriguez Cigar Factory.

Though family-friendly, The Gates isn’t the place for those hungry for silence. The hotel’s social scene revolves around Rum Row, the bar and lounge circling the L-shaped pool. Days bring shaded cabanas and tapas-style lunches (say, ceviche and shrimp skewers), while most nights bring DJs and a perma-flow of rum sourced from nearby Key West Rum Distillery.

And, while it may be a small luxury, the hotel-wide free WiFi is as refreshing as the gulf breeze that ruffles the poolside palms.